50 Best Bermuda Vacation rentals on Holiday Lettings - Estates

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Pembroke Parish
13 properties
Southampton Parish
12 properties
Smith's Parish
11 properties
St. George's Parish
10 properties
Sandys Parish
8 properties
Warwick Parish
5 properties
Hamilton Parish
5 properties
Paget Parish
5 properties

Bermuda

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69 Vacation rentals

(6) Excellent 

12

South Shore Vacation apartment rental

Southampton Parish / South Shore

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
A contemporary ocean-front apartment with access to a horizon pool located at the end of a quiet lane on the south shore between West Whale Bay and Church Bay. Ideal for those looking to relax, with panoramic ocean views from every room and a private lawn where you can …see more

from $295 / night

$2,065 / week

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from $295 / night

17

Bermuda Vacation studio rental

Bermuda / Southampton Parish

Studio 2 2 nights min

  • Studio
  • Sleeps 2
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Private and cozy studio located on a hill which gives you a breathtaking view of Jews Bay and Dockyard (home of the Americas Cup). The studio is part of a large house with a separate entrance. It is fully furnished - comfortable queen size bed, love seat, dining for 2, …see more

from $150 / night

$1,050 / week

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from $150 / night

25

Bermuda Vacation home rental

Bermuda / Paget Parish

7 14 1 night min

  • 7 bedrooms
  • Sleeps 14
  • 1 night min
  • Child friendly
Sprawling graciously , in a park like setting, filled with grand old majestic trees, sits this five bedroom five and a half bathroom entertainer's paradise. Behind the enchanting traditional Bermuda façade lies a modern interpretation of sophisticated and care-free urba …see more

from $922 / night

$10,936 - $14,525 / week

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from $922 / night

(1) Excellent 

22

Vacation home in Bermuda

Bermuda / Warwick Parish

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 3 mi
  • Child friendly
  • Car not necessary
The house is tucked privately off of the main South Shore Road in Bermuda. It is in a beautifully, safe location that is walking distance to restaurants, a one-stop gas station, the best beaches and public transportation. This unit is a 2 bedroom apartment that rents fo …see more

from $169 / night

$1,183 / week

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avg. 2 hours 24 minutes

from $169 / night

14

Vacation cottage in Bermuda

Bermuda / Southampton Parish

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Ask about children
  • Air conditioning
Adorable stand alone cottage located in Southampton with stunning views of the Great Sound. The cottage itself consists of two bedrooms, one bathroom, eat-in kitchen, a living room with fireplace, a covered porch and a lower level laundry room. The cottage has two acces …see more

from $197 / night

$1,379 / week

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avg. 2 hours 51 minutes

from $197 / night

(3) Excellent 

9

Vacation home with shared pool in Smith's Parish

Bermuda / Smith's Parish

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Swimming pool
  • Air conditioning
The pool house is a studio and has a queen bed and its own bathroom + shower. It is next to our house in a spacious yard in a quiet residential neighborhood. Bus stop is a 3 minute walk, beautiful John Smith's Bay beach is a 5 minute walk and a grocery store is a 10 min …see more

from $120 / night

$770 - $1,085 / week

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avg. 1 hour 14 minutes

from $120 / night

20

Bermuda Vacation home rental

Bermuda / Southampton Parish

4 12 3 nights min

  • 4 bedrooms
  • Sleeps 12
  • 3 nights min
  • Child friendly
The Four C's is situated in a prime location for vacationers. Situated just off of the South Shore Road between Horseshoe Bay Beach and Church Bay Beach only a very short walk to Cross Bay Beach your private beach, where you can enjoy endless hours in the Sun and Surf. …see more

from $680 / night

$4,760 / week

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from $680 / night

17

Bermuda Vacation home rental

Smith's Parish / Flatts Village

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
  • Ask about children
  • Air conditioning
The private cottage is a true getaway. Nestled on the shore above Flatt's inlet, the outdoor spaces alone are a true treasure. The home enjoys a covered porch overlookin the turquoise waters of Flatt's inlet, as well as having water access for swimming and snorkeling, a …see more

from $259 / night

$1,813 / week

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avg. 2 hours 51 minutes

from $259 / night

(2) Excellent 

22

Vacation studio with swimming pool, tennis court in Paget Parish

Bermuda / Paget Parish

Studio 2 5 nights min

  • Studio
  • Sleeps 2
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
•Consistently rated 5★★★★★ •Your OWN Private Pool & Tennis Court •Walk to Hamilton •5 min. ride to Elbow Beach •High speed Internet •New Pillow-top, king-sized bed •Fully equipped + stocked kitchen •Near bus stops to both ends of the island •42" TV •Extremely safe neigh …see more

from $149 / night

$1,043 / week

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avg. 2 hours 52 minutes

from $149 / night

14

Vacation cottage in Bermuda

Bermuda / Southampton Parish

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Ask about children
  • Air conditioning
Adorable stand alone cottage located in Southampton with stunning views of the Great Sound. The cottage itself consists of two bedrooms, one bathroom, eat-in kitchen, a living room with fireplace, a covered front porch, and a private back porch. The cottage has two acce …see more

from $230 / night

$1,610 / week

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from $230 / night

7

Vacation home in Bermuda

Bermuda / Sandys Parish

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Ask about children
  • Air conditioning
This immaculate studio apartment has been recently built with modern amenities. Located close to the main bus route, for easy access to Dockyard (5 minutes) and Hamilton (40 minutes), this residential neighborhood is your perfect home away from home. The bedroom is furn …see more

from $140 / night

$980 / week

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from $140 / night

(1) Excellent 

10

Vacation apartment with shared pool in Bermuda

Bermuda / Smith's Parish

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Swimming pool
  • Air conditioning
  • Private garden
The apartment is close to the beautiful John Smiths Bay beach - an 8 minute walk away. The pool is on the property and around the back from the apartment. The apartment has a queen bed and its own bathroom + shower. It is next to our house in a spacious yard in a quiet …see more

from $120 / night

$770 - $1,050 / week

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avg. 1 hour 14 minutes

from $120 / night

7

Vacation home with shared pool in Paget Parish

Bermuda / Paget Parish

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Only steps from Hamilton, this self-contained apartment on the pool level enjoys an amazing view down the harbour and across the Great Sound, while being walking distance from restaurants and shops in Hamilton. Public transportation is close by, providing access to the …see more

from $210 / night

$1,470 / week

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from $210 / night

7

Vacation home in Hamilton

Pembroke Parish / Hamilton

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Ask about children
  • Air conditioning
Loquat Master is a lovely studio apartment situated in the perfect location. On the main bus route, and within walking distance to restaurants grocery store and Bermuda's most beautiful beach- Horseshoe Bay- what more could you ask for? The studio is on the upper level, …see more

from $100 / night

$700 / week

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from $100 / night

(10) Excellent 

17

Vacation home in St. George

St. George's Parish / St. George

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 0.5 mi
  • Ask about children
  • Car not necessary
1768 historic Bermuda cottage, restored with modern conveniences, situated in the Town of St George and just walking distance to beautiful beaches and historic forts as well as restaurants and shops. Cottage is set in a landscaped garden with tropical fruit trees and ea …see more

from $195 / night

$1,365 / week

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Responds fast!
avg. 36 minutes

from $195 / night

(4) Excellent 

15

Vacation home in Bermuda

St. George's Parish / Tucker's Town

2 4 30 nights min

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min
  • Air conditioning
  • Private garden
This house sits on the Mid-Ocean Golf Club between the 16th and 17thh fairways in Bermuda overlooking Castle Harbour and the outlying islands. There are 2 bedrooms with bathrooms ensuite, one with king sized bed and the other with queen sized bed. There is also a powde …see more

from $275 / night

$1,925 / week

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from $275 / night

17

Home rental in Somerset Village

Sandys Parish / Somerset Village

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Pet friendly
Welcome to our fully equipped + furnished beach front condo! My mission is to make sure your island experience an unforgettable one so please reach out if you have any questions. The condo is fully furnished ft. High-quality furniture, 180-degree ocean views for beaut …see more

from $400 / night

$2,800 / week

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from $400 / night

(10) Excellent 

Certificate of Excellence

12

Vacation apartment in Bermuda

Bermuda / Pembroke Parish

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning
Lemon and Ginger Vacation Rental is a centrally located one bedroom apartment in Pembroke, Bermuda. Visit Bermuda and live like the locals do in a safe, family-like neighborhood. Located on the north side of Bermuda amongst two spectacular parks, with caves that you ca …see more

Certificate of Excellence

from $135 / night

$945 / week

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Responds fast!
avg. 1 hour 35 minutes

from $135 / night

(1) Excellent 

23

Apartment rental in Bermuda

Bermuda / Smith's Parish

1 5 3 nights min

  • 1 bedroom
  • Sleeps 5
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
Large one bedroom apartment located off of Knapton Hill in Smith's in a very private neighborhood. Very spacious and in a private garden setting. Lovely to sit off on the patio after a long day at the beach or out on the water. Galley Kitchen opening up onto large li …see more

from $155 / night

$1,085 / week

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avg. 3 hours 34 minutes

from $155 / night

25

Vacation home rental

Bermuda / Southampton Parish

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Ask about children
  • Air conditioning
This lovely waterfront home has stunning views of the Great Sound and consists of 4 bedrooms with 4 bathrooms. The master bed with a king bed, two guest rooms with two twins and the other guest room with a double bed. There is a large formal living room with wood burnin …see more

from $777 / night

$5,439 / week

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from $777 / night

(1) Very Good 

32

Vacation apartment in Bermuda

Bermuda / Hamilton Parish

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Car not necessary
  • Air conditioning
Attractive lower apartment on a property with panoramic seascape views of North Shore Bermuda. Extra features include excursions to Bermuda Railway trail, fishing off of Bay Island, visits to nearby Crystal Caves (we are descendants of the discoverers) and Grotto Bay Ca …see more

from $90 / night

$630 / week

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avg. 2 hours 50 minutes

from $90 / night

(7) Excellent 

18

Vacation b&b in St. George

St. George's Parish / St. George

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 2 mi
  • Car not necessary
  • Air conditioning
Aunt Nea's Inn is a historic Bermudian guest house located in the UNESCO World Heritage site of St. George's. From original woodwork and building craftsmanship from the 1700s to stunning harbour and garden views, you will love staying in this very special property in th …see more

from $195 / night

$1,365 / week

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from $195 / night

(16) Very Good 

10

Vacation cottage in Bermuda

St. George's Parish / St. George

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.8 mi
  • Child friendly
Experience your Bermuda vacation in the World Heritage Town of St Georges! This traditional Bermuda cottage has been thoroughly updated and modernized whilst retaining charm and character. Amenities include an en-suite master bedroom with King size bed, a modern fully …see more

from $175 / night

$1,250 / week

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from $175 / night

(16) Excellent 

Certificate of Excellence

15

Bermuda Vacation home rental

Bermuda / Warwick Parish

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Sunscape Bermuda is a handsome house standing on top of Lusher Hill exhibiting breathtaking views of the entire island. It is only 5 minutes by moped to the beautiful sands of Warwick Long Bay and just a stroll from there to the Horseshoe Bay. The parish of Warwick is r …see more

Certificate of Excellence

from $200 / night

$1,400 / week

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Responds fast!
avg. 3 hours 46 minutes

from $200 / night

5

Cottage rental in St. George

St. George's Parish / St. George

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
Two bedroom timeshare cottage at St George's Club overlooking St George Town, a UNESCO World Heritage site. Available 7 nights from Saturday August 12th to 19th, 2017. Unit #32 sits on a hill with beautiful views of historic St George harbor. Has 2nd floor master be …see more

from $422 / night

$2,950 / week

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from $422 / night

25

Vacation home in Bermuda

Bermuda / Southampton Parish

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Ask about children
  • Air conditioning
This lovely waterfront home has stunning views of the Great Sound and consists of 4 bedrooms with 4 bathrooms. The master bed with a king bed, two guest rooms with two twins and the other guest room with a double bed. There is a large formal living room with wood burnin …see more

from $893 / night

$6,251 / week

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Responds fast!
avg. 2 hours 51 minutes

from $893 / night

(5) Very Good 

12

Apartment rental in Hamilton Parish

Bermuda / Hamilton Parish

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Child friendly
'Neston' is on 2 acres of property, located in a very quiet and secluded neighborhood. Enjoy the Beautiful Views of Harrington Sound one of the most Beautiful inlets in Bermuda. Harrington Sound is a wonderful inland lake in Bermuda surrounded mainly by Hamilto …see more

from $195 / night

$1,365 / week

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from $195 / night

(11) Excellent 

31

Vacation home in Southampton Parish

Bermuda / Southampton Parish

2 2 nights min

  • Sleeps 2
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
Located on a hill with simply breathtaking views of Jews Bay. The studio is part of a large house with a separate entrance, located within walking distance of the pink and silver sands of Horseshoe Bay Beach and Church Bay, the Gibbs Hill Lighthouse, the Railway Trail, …see more

from $110 / night

$770 / week

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avg. 1 hour 30 minutes

from $110 / night

10

Vacation home in Pembroke Parish

Bermuda / Pembroke Parish

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
  • Air conditioning
This spacious apartment is located only minutes from the capital city of Hamilton. Walk to the grocery story (2 minutes), ferry (10 minutes) or shops and restaurants (10 minutes) while enjoying the tranquility of the surrounding Fairylands neighborhood. The apartment ha …see more

from $300 / night

$2,100 / week

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from $300 / night

26

Vacation studio in Bermuda

Sandys Parish / Somerset Village

Studio 4 4 nights min

  • Studio
  • Sleeps 4
  • 4 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
This studio sits in the heart of Somerset Village in Sandys, Bermuda. Easily an ideal place for couples visiting Bermuda without transportation. Its the perfect spot with a restaurant across the street, local shops, beaches, bus stops and other entertainment within clos …see more

from $200 / night

$1,400 / week

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from $200 / night

13

Bermuda Vacation cottage rental

Sandys Parish / Somerset Village

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Ask about children
  • Air conditioning
Litt Ends Cottage sits perched about the waters of Jews Bay, with pictureque views across Granaway Deep and Dockyard. Located in Southampton, it is within walking distance to the Fairmont Southampton (restaurants and spa), moped rental, boat and jet ski rentals, and the …see more

from $202 / night

$1,414 / week

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from $202 / night

(2) Excellent 

16

Apartment rental in Bermuda

Bermuda / Warwick Parish

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
This beautiful property is located on the South Shore close to all the popular beaches and directly across from Warwick Long Bay which was listed by CNN as one of the top beaches in the world. This unit is just steps away from the bus stop and the playground ... for tho …see more

from $250 / night

$1,680 / week

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avg. 2 hours 58 minutes

from $250 / night

12

Vacation b&b in Bermuda

St. George's Parish / St. George

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Aunt Nea's Inn is a historic Bed & Breakfast in the Town of St. George's. Put your feet up and truly unwind in our Green Turtle room, featuring a separate bedroom and living area with kitchenette. The bathroom features a rain shower located off of the bedroom with a se …see more

from $225 / night

$1,575 / week

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from $225 / night

6

Apartment rental in Hamilton

Pembroke Parish / Hamilton

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
Relax on the porch and enjoy the view of one of the most beautiful harbours in the world. These apartments are situated in a quiet secluded neighborhood that can be enjoyed by foot to explore its beautiful homes, gardens, and bays. Minutes away by moped or taxi are the …see more

from $135 / night

$900 - $1,500 / week

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avg. 2 hours 30 minutes

from $135 / night

(7) Excellent 

4

Vacation studio with shared pool in Bermuda

Pembroke Parish / Hamilton

Studio 2 4 nights min

  • Studio
  • Sleeps 2
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 8 mi
  • Swimming pool
Hibiscus Hideaway is a self-catered, studio accommodation for tourists and business travelers, located in a serene and very convenient location. A pleasant 5-minute walk into the heart of Hamilton, making all of the amenities easily accessible (shops, restaurants, groce …see more

from $150 / night

$1,050 / week

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from $150 / night

5

Vacation home in Hamilton

Pembroke Parish / Hamilton

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Ask about children
  • Air conditioning
Loquat Lower is a lovely studio apartment situated in the perfect location. On the main bus route, and within walking distance to restaurants grocery store and Bermuda's most beautiful beach- Horseshoe Bay- what more could you ask for? The studio is on the lower level, …see more

from $75 / night

$525 / week

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from $75 / night

16

Vacation home in Hamilton Parish

Bermuda / Hamilton Parish

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Air conditioning
  • Private garden
Pigeon View Cottage is named after the spectacular view of Pigeon Island in Bailey's Bay. The property is conveniently located near to the airport and to various attractions such as Crystal Caves, Swizzle Inn, Jamaican Grill Restaurant, Tom Moore's Jungle and Tavern, Ra …see more

from $180 / night

$1,200 - $2,320 / week

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avg. 2 hours 50 minutes

from $180 / night

(14) Excellent 

20

Vacation b&b with shared pool in Bermuda

Bermuda / Smith's Parish

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
PLEASE NOTE WE DO NOT ACCEPT CHILDREN PLEASE ASK ABOUT YOUNG ADULTS. Watch Hill Manor B & B Suites are conveniently located in Smith's Parish, only 12 minutes from the Bermuda's International Airport. The property is well situated on Watch Hill, on Knapton Estates Roa …see more

from $220 / night

$1,540 - $1,855 / week

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from $220 / night

(1) Excellent 

17

Bermuda Vacation studio rental

Sandys Parish / Somerset Village

Studio 3 4 nights min

  • Studio
  • Sleeps 3
  • 4 nights min
  • Child friendly
  • Air conditioning
This studio sits in the heart of Somerset Village in Sandys, Bermuda. Easily an ideal place for couples visiting Bermuda without transportation. Its the perfect spot with a restaurant across the street, local shops, beaches, bus stops and entertainment within close prox …see more

from $200 / night

$1,400 / week

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from $200 / night

7

Vacation home in Bermuda

Bermuda / Paget Parish

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Ask about children
Only steps from Hamilton, this self-contained apartment on the pool level enjoys an amazing view down the harbour and across the Great Sound, while being walking distance from restaurants and shops in Hamilton. Public transportation is close by, providing access to the …see more

from $235 / night

$1,645 / week

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Responds fast!
avg. 2 hours 51 minutes

from $235 / night